Starting out as a wrestler in Canada in 1979, he failed miserably due to poor training and retired quickly with a knee injury and moved on to run a night club but came back to AWA, albeit as a manager, managing BADD COMPANY and led them to tag team titles. He also managed Col Debeers, Curt Hennig in what was called Diamond Exchange, adding the name Diamond as his trademark catch word going on to coin Diamond Dolls to his valets.
He failed to get a job in WWF in 1990 and joined WCW where he managed The Fabulous Freebirds, Diamond Studd (Scott Hall) while also working as Colour Commentator. Based on what he heard about his priced star, Diamond studd, being taken away from him by WCW to a change of character, as per Magnum T.A's advice decided to become a wrestler again and headed straight to Power Plant at 35 years of age in 1991-92 and made a debut as Scott Hall's partner against Sullivan's team but was soon relegated to jobber status.
Then he created Diamond Mine, a stable of Raven and Nash and redebuted as a wrestler when he teamed with Nash in Vegas Connection, the moment they relived as Insiders years later. Nash left for WWF and Page injured himself leading to getting fired.
Then he turned to none other than Jake the snake Roberts who molded his character, taught him the psychological aspects during his recuperating period. He debut again in WCW with Kimberly as his valet and got involved in various feuds giving his raise to WCW TV championship and started to take on NWO and slowly rose to the DDP we all know; the US, tag and World Heavyweight champion.
He then moved into WWF, 10 years after he was rejected a job, had a feud with non other than the Taker, before being delegated again to Jobber status and then moving on to TNA, JCW and retiring eventually. He then went on to become a motivational speaker, Fitness Guru and trademarked the self Hi-five which won him some money in lawsuits.
He is mostly known for all this variations of Diamond Cutter which he managed to pull off from various positions during his matches and playing the villain in the movie Ready to Rumble and 14 titles to his name of which 11 were in WCW.
He epitomizes the never say die attitude rising again every time he was put down doing what was necessary and changing himself.